Gwyneth Paltrow’s Bold and Controversial Red Carpet Fashion Choices

The Oscars are notorious for being one of the most formal events in the world, with attendees dressing to the nines in tops, tails, and ballgowns. But Gwyneth Paltrow’s 2000 Calvin Klein dress was totally underwhelming — and even she knew it. “It’s an okay dress but not Oscars material. I chose it because I wanted to disappear that year,” she admitted 13 years later in a Goop blog (via Fashionista). Though the irony was that by underplaying her outfit, the “Shallow Hal” star stood out more.

While we appreciated that Paltrow at least tried to assimilate with the dress code via the shimmery material, the light gray shade washed her out. The gown’s hem also needed to be longer to make it more formal. Equally, the long, orange beaded necklace with tassels didn’t match the garment’s aesthetic and was distracting.

Gwyneth Paltrow made everyone stop and stare when she hit the “Iron Man 3” red carpet in 2013 in a structured, fashion-forward dress with sheer panels that went from her thigh down to her toe. The dress was risky in a good way and would have been perfect for the premiere of a rom-com. However, it felt inappropriate considering superhero movies have young fans. Paltrow also went commando under the garment and had to be extra careful when being photographed from the side.

“I kind of had a disaster. I was doing a show and I changed there, and I went and I couldn’t wear underwear … Well, let’s just say everyone went scrambling for a razor and so I went from being the most beautiful to the most humiliated in one day,” she said on “The Ellen DeGeneres Show” (via TV Guide).

In 2008, Gwyneth Paltrow risked what could have been a multiple wardrobe malfunctions during a hotel opening in Miami. She wore a strapless, white mini dress with a plunging sweetheart neckline that practically grazed the top of her stomach. Had she pulled the dress down slightly, her chest would be totally exposed, while one slight pull upwards would likely have flashed her undies. And that didn’t leave much room for free movement.

Paltrow’s slightly stiff pose on the red carpet gave the impression the dress’ fit wasn’t comfortable as the fabric appeared tight around her waist. Equally, the extra material over her torso and the gathers on her hips created an awkward shape, while the skirt’s material appeared cheap as it was slightly see-through and showed the outline of her legs.

Gwyneth Paltrow got it wrong at the 2002 Oscars, too. She wore a sheer-illusion top dress with a long, black skirt that felt more ‘done’ than her 2000 dress, but the Alexander McQueen look still didn’t bring the glam we’re used to seeing on such a big red carpet. She later explained in a Goop post, “I should have worn a bra and I should have just had simple beachy hair and less makeup. Then, it would have worked as I wanted it to — a little bit of punk at the Oscars.”

Not pairing the look with the appropriate underwear meant Paltrow showed more skin than she intended. Though we’re all for freeing the nipple when the moment is right, the Oscars didn’t feel like the right place to make such a statement — especially in 2002, when the movement wasn’t so widely acknowledged.

From no underwear to too much underwear, Gwyneth Paltrow made the opposite faux pas in 2008 at the “Two Lovers” premiere. She wore a black-and-white spaghetti strap dress with sheer, lace down the middle. Though the dress had potential to be one of her spiciest looks ever and would have worked perfectly for the 2023 sheer dress trend revival, Paltrow’s execution was off. She seemingly wore a white bra and panties underneath, which became glaringly obvious in the paparazzi flashes.

Though we understand the actor wanting to stay covered in the revealing gown, barely there, nude undergarments with thin straps, or black undies, would have been a chicer choice. After all, visible underwear can give the wrong impression and is a fashion mistake that’s a complete turn-off.